


Mommy Dearest

by orphan_account



Category: Supernatural
Genre: Barebacking, Cock Cages, Cock Rings, Cock Tease, Dom Mary Winchester, F/M, Femdom, Incest Kink, Light BDSM, Mommy Kink, Oral Sex, Orgasm Denial, Parent/Child Incest, Plot What Plot/Porn Without Plot, Rough Sex, Smut, Squirting, Sub Dean Winchester
Language: English
Status: Completed
Published: 2017-06-03
Updated: 2017-06-03
Packaged: 2018-11-08 11:20:35
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,598
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11080500
Author URL: https://archiveofourown.org/users/orphan_account/pseuds/orphan_account
Summary: Two weeks of playtime with Mary sounded like heaven for Dean. That was, until she decided it'd be an excellent time to test how strong her son's willpower was.





	Mommy Dearest

**Author's Note:**

> Written for SPN Kink Bingo 2017  
> Square Filled: DeanMary

“Please, Mom, I—I can’t take this anymore,” Dean whispered, his eyes fluttering shut. Mary crouched down, stroking her thumb over his flushed cheek.

“Yes, you can, Dean. You’re a strong boy.”

Dean sobbed brokenly, chasing her touch when she pulled away. He hung his head, staring at the concrete floor of his bedroom. His cock bounced between his thighs, the cool air of the room barely affecting the heated, flushed skin. The tip was a deep red, balls drawn tight to his body despite the ring keeping him from falling over the edge into his much-needed climax. One full week he’d been denied orgasm. The calendar on the wall in front of him was taunting him, bright red x’s on the days he’d been a  _ good boy _ and behaved. Seven fucking days of torture.

Every night locked in a chastity cage, every day spent pleasing his mom and trying his hardest not to come.

They still had one week left alone before Sam returned from his trip. And Dean knew his Mom intended to push him to his limits. See just how  _ far _ he could go.

Mary circled around Dean, her nails tickling the hypersensitive skin on his shoulders and the back of his neck.

“Go lie on the bed, Dean.”

“Mom, please let me come,” Dean whispered, rising to his feet. He padded over to the bed and stretched out, allowing Mary to tie his arms and legs to the frame spread eagle.

While she was strapping his arms up, Dean leaned forward, catching her nipple in his mouth. He gave a hard suck, his cock jerking at the moan it pulled from her lips. 

She looked down, stroking her fingers through his hair. "Good boy, making sure I feel good?" Dean nodded, nibbling lightly between sucks, rolling his eyes up to look at her. 

"Patience, sweetheart, and I'll give you something better." She finished tying his wrists before moving up, straddling his head. 

Dean inhaled deeply, the sweet, musky scent of her arousal surrounding him. 

"Mom," he begged. She sank down over his open mouth, gasping when he drove his tongue into her pussy immediately, twisting and turning his head.

He knew the deal by now. The closer he got her to orgasm with his mouth, the less she'd torture his cock. 

He closed his eyes and dove in, swirling his tongue around her swollen clit and driving it deep inside her, lapping at her slick inner walls. His hands were formed into tight fists, straining against the ropes; he wanted so badly to grab her hips, pin her on the bed and drive fingers and tongue into her until she screamed.

Mary ground down on his face, forcing his tongue a little deeper. Her fingers knotted in his short hair, yanking upwards. Each tug sent sparks to his cock, making it twitch against his heaving stomach. She pulled back much too soon for Dean’s satisfaction, leaving him chasing her body with his mouth open, lips and chin wet with her fluids.

“Please, Mom—You gotta let me come this time,” Dean panted when Mary slid down his body, grinding against his cock.

“I don’t think so, needy little boy. I think you need to earn it still.”

Dean groaned, throwing his head back onto the pillow. Mary shifted, reaching between them and grabbing his cock in a painfully tight grip. His lips twisted downward, embarrassed at how much his balls throbbed even with a painful touches. Needy was an understatement.

They moaned in unison when Mary sank down, her wet heat clenching around him. Dean screwed his eyes shut, forcing himself to breathe through his nose. 

"Oh, Dean-- Such a big cock," Mary panted as she rode him quickly. "Bigger than your father was. You know just how to make your Mom feel good." 

Dean grunted, his cock jerking at her words. He felt a blurt of precome dribble from his aching tip, only to be spread around Mary's insides as she rocked down onto him. 

Somewhere in the back of his mind he was aware of how twisted this was, the woman that carried him for nine months riding his cock until it ached - but the life of a hunter was twisted anyways. 

"Mom-- Mom, I'm gonna come," Dean warned, tugging his restraints. When she didn’t slow down, a glimmer of hope rose in his stomach. Was she going to let him come? He closed his eyes, letting the feeling wash over him. So close, just one or two more—

Dean screamed in frustration when Mary pulled off his cock at the last second, leaving him jerking his hips into the air fruitlessly.

“Mom!” He sobbed, looking over at her. Her eyes were closed, fingers working her clit as quickly as she could. Dean whimpered when she came with a cry of his name, squirting onto the bed and down her quivering thighs. She slumped down, placing her palms on the bed near Dean’s side, breathing hard.

“Please—“ He tried again.

Mary looked up, smiling a little. Her blonde hair fell around her face in a messy frame, cheeks mottled red and forehead damp.

“That felt great, son. Thank you. I think it’s time for dinner now.” She unhooked his wrists and legs and flicked his cock at the tip, ignoring his whimpers until he softened up enough for her to slip the cock cage back on.

One more week.

Dean was starting to worry she’d  _ never _ let him come.

***

Two days remained before Sam would be back in the bunker and Mary and Dean would have to be quiet about their relationship once more. Dean knew Sam had suspicions, but he was respectful enough not to pry, and Dean didn’t want to scar his little brother for life.

Two days, and Mary  _ still _ held him in chastity and denial. It was mechanical now. Let Mary tie him up, try his hardest to make her come, let her ride him, back in chastity. Not that it wasn't pleasurable - quite the opposite, much to Dean's surprise. It hurt like hell sometimes; the constant edging, the teasing - but Dean felt a strange sense of pride. 

He was being good. He was doing what his Mom asked and he was making her happy. His cock throbbed at the mere thought of seeing her smile like she did when Dean resisted yet another orgasm. 

That's where they were - Dean's tongue deep in Mary's pussy, slick wet sounds as he sucked her clit and damp folds. His cock was leaking onto his stomach, each tug of her hands in his hair igniting a fire in his swollen balls, but that wasn't Dean's focus.

He'd improved his skills in oral pleasure. Always a point of pride for him, now he could almost get her to the edge before time was up. Today, Dean hoped, today would be the day he tasted her fresh, coming on his face instead of his cock. 

Mary was writhing, clenching around Dean's tongue as he let his nose bump against her clit, his stubble scraping against her smooth skin. He could feel her getting wetter, dribbling onto his tongue as he swirled it around. Leaning back, Dean let his chin scrape across her opening, catching her clit between his teeth. Mary looked down and Dean winked before beginning to suck in earnest, his tongue flicking and jabbing from different angles each second. 

Mary's body went stiff, her thighs squeezing Dean's head as she screamed. 

He moved down, sealing his lips over her opening as she came, squirting hot and wet streams against his tongue. He nosed her clit, allowing her to rub herself while he lapped at her opening with wide, broad strokes, letting the fluid gather in his mouth. 

When he felt no more, Dean pulled back, holding his mouth open so she could see before swallowing it, smiling and placing a chaste kiss to her clit. 

"You taste so good, Mom. Come again for me, please. Use your little boy's cock to make yourself come again. I'll be good," he promised. 

Mary smiled a little. She slid down his body, lifting his cock and sinking onto it without hesitation. 

Dean grunted, gritting his teeth. Tasting her had pushed him closer to the edge than he expected, his balls throbbing tight against his body at her slick heat. 

"Mom-- I'm sorry," he whispered, "I'm already close."

Mary continued to ride him, giving no indication she heard his warning. But Dean knew she did. Yet another part of the mechanics - she'd ride his cock until the last second and pull off, leaving him sore and aching yet again. 

Expecting it didn't make it hurt less. Dean sobbed brokenly when she pulled off his cock, watching it give a weak dribble of come. 

Instead of releasing him, however, Mary turned and walked to the door. 

"What are you doing, Mom?" Dean asked softly. 

"Waiting, sweetheart. You asked me to come on your cock, I'd like to do that. But you need to calm down a little. I'll be back." 

With that she walked out, leaving him alone. 

When Mary returned, she slapped Dean's cock, startling him into opening his eyes. 

"Don't sleep, naughty boy - you don't have your cage on."

Dean bit his lip, his cock thickening fully at the sight of his naked mother once more.

Mary straddled his hips and sank back down on his cock, leaning forward as she began to ride him. 

Ten minutes. Dean managed ten minutes of her clamping down on his cock, the wet sounds of their sweat soaked skin hitting, the soft moans of how nice Dean was to her before it was too much. 

He opened his mouth to warn her, his cock throbbing dangerously, but Mary was already pulling off. Dean’s body slumped, shaking his head.

“So close,” Mary praised, stroking his cheek. “Once or twice more and I’ll come, baby.”

“Please, Mom—I can’t hold on like that two more times,” Dean pleaded.

“Yes, you can. And you will. Don’t fall asleep.” She patted his head before leaving the room again.

The third time was torture. Dean was on edge the second he could feel the heat from Mary’s body over his cock, and he was only able to last five minutes before she was forced to pull off, soothing his whimpers with a gentle hand on his heaving chest.

“You’ll get it, Dean.”

“Mom, please,” Dean whispered, tugging at the ropes around his wrist.

“No. I’m going to leave you a little longer – do I need to put you in your cage or will you behave?” She asked. Dean swallowed audibly and shook his head.

“I’ll behave. I just don’t think I can last long enough for you to come, I’m so sorry—“

“Don’t be silly. We’ll try one more time, okay?”

Dean nodded, letting his eyes slip shut. He barely heard the door shut, focusing on his breathing and relaxing his aching body and nerves.

Mary didn’t return for nearly half an hour this time, giving Dean’s body enough time to step back from the edge – at least as much as it was going to in his current condition.

He was staring up at the ceiling when the door opened, thinking of the most grotesque cases he and Sam had ever been on. Anything to stave off the aching need to come.

“Ready, Dean?” Mary’s voice was soft. He looked over, his throat clicking.

“Yeah,” he whispered.

“Does it hurt too much, baby? You can give up if you need to.”

“I don’t give up, Mom. Never have,” Dean said, hardening his expression and turning his head to look up at the ceiling again. “Let’s try this again.”

Despite his determination, Dean broke. Mary was wet, her pussy dragging along his cock and lighting the fire in his belly once more. He shook his head, doing everything he could to ignore the pressing need to come, the tightness of his aching balls, the steady dribble of precome.

The sound of blood rushing in his ears was overwhelming, every nerve in his body burning hot with invisible fire. Dean's legs quivered as Mary rode him. Tears of pain and pleasure slipped down his cheeks before he could blink them away, and he sobbed weakly. "I can't, Mommy, I-- I gotta come,  _ please _ ," he whispered.

Mary's hips stuttered against him and she clamped down on his cock. 

"Say that again, baby," she asked. 

Dean scowled for a second, then smirked. "Lemme come, Mommy."

Mary moaned, splaying her hands on his chest as she began to ride him faster. She came hard, clenching around him as the rest of her body stiffened, head thrown back as she called his name. 

Dean could feel her come dribbling down the part of his cock not buried in her, wetting his balls and the sheets between his open thighs. He jerked his hips up as high as he could, driving deeper into her. 

Mary gasped, looking down. Her eyes were hazy with lust, full lips parted as she came down from her orgasm. "You wanna come, Dean?"

"Please, Mommy," he whispered, shivering when she clenched again. 

She pulled off his cock and removed the ring before untying his hands and ankles. Sitting back on the bed between his legs, Mary spread her thighs, giving him a perfect view of her swollen, red folds, her hole barely visible. 

"Then come, baby boy."

Dean's eyes widened. "Really?" He asked, half expecting a trick. 

"Really. Come on."

Dean sprang into action. He pinned Mary on her back under him, kissing her hard as he drove his aching cock deep into her. 

Mary screamed into his mouth, her nails drawing blood as she scraped them down his back and ass. 

Not wasting a second, Dean pounded into her, feeling her squirt around his cock. He bit down on her earlobe. 

"I'm not pulling out," he warned, surprised to feel Mary's legs clamp around his hips. 

"Wouldn't let you," she said. "Give it all to Mommy, Dean. Come on."

Dean groaned, twisting his hips to drive deeper. All too soon he felt his orgasm approaching. 

"I'm gonna come," he warned, half expecting her to push him off. 

Instead, her legs tightened around him and she dug her fingers into his shoulders, looking up at him with a smile. 

Dean drove in twice more, burying his cock as deep as he could get it before he came, his entire body jerking with the force. He could hear Mary screaming for him, but her voice was far off, muffled. Every muscle in his body twitched, a dull ache settling in his lower back with the tension gathering there.

It took nearly twenty minutes for Dean to relax, his shoulders slumping before rolling to the side of Mary. He whimpered when his spent cock slipped out, hypersensitive and sore. 

They exchanged a glance before they both started chuckling, Mary’s hand drifting over to squeeze Dean’s.

“Are you alright?” He worried, reaching over and placing his free hand on her stomach.

“I’m perfect, baby.”

“I went a little rough—“

“It was exactly what I wanted. I didn’t push you too far did I?”

Dean grinned and shook his head. “Nah, it was awesome. A mommy kink, huh?” He teased, smiling wider when Mary’s cheeks reddened.

“I didn’t know I had it.”

“You most certainly do. We’ll have to explore that a little more next time Sammy goes away for a few days.”

Mary shook her head, smiling softly. She leaned up, pulling Dean in for another kiss.


End file.
